WO2017197739A1 - 有机电致发光材料及有机电致发光器件 - Google Patents

有机电致发光材料及有机电致发光器件 Download PDF

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WO2017197739A1
WO2017197739A1 PCT/CN2016/088498 CN2016088498W WO2017197739A1 WO 2017197739 A1 WO2017197739 A1 WO 2017197739A1 CN 2016088498 W CN2016088498 W CN 2016088498W WO 2017197739 A1 WO2017197739 A1 WO 2017197739A1
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organic electroluminescent
electroluminescent material
hydrogen atom
alkyl group
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谢华飞
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TCL China Star Optoelectronics Technology Co Ltd
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Shenzhen China Star Optoelectronics Technology Co Ltd
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Definitions

  • the present invention relates to the field of display technology, and in particular to an organic electroluminescent material and related organic electroluminescent device.
  • organic electroluminescent materials In organic electroluminescent technology, the choice of organic electroluminescent materials is crucial, and its nature is one of the key factors determining device performance. At present, organic electroluminescent materials mainly use organic small molecule compounds or polymers, which have strong chemical modification, wide selection range, easy purification, high fluorescence quantum efficiency, and can produce various colors such as red, green and blue. specific.
  • organic dyes have a problem of concentration quenching in the solid state, which will lead to defects such as broadening of the emission peak of the device, red shift of the spectrum, and decrease in fluorescence quantum efficiency. Therefore, they are generally doped at the lowest concentration.
  • a trace amount of the organic fluorescent dye is dispersed in the matrix of the main illuminant by the principle of energy transfer, so that the guest molecule can emit light by the transmission of the excitation light energy. Therefore, most of the high-performance organic electroluminescent devices reported so far have adopted a method of preparing a light-emitting layer doping.
  • the preparation method of such doping requires precise regulation to ensure the accuracy of the doping concentration, which will increase the manufacturing cost and is not conducive to the industrialization of the organic electroluminescence technology.
  • the phase separation and energy transfer of the host and guest in the doped device also affect the performance and stability of the device.
  • the organic electroluminescent non-doped device can avoid the influence of the doping concentration, which enhances the stability and repeatability of the device, and effectively prolongs the life of the device. It reduces the difficulty of the processing technology and is suitable for large-scale commercial production.
  • high-performance undoped luminescent materials require high-efficiency solid state at the same time. Such harsh characteristics such as luminescence, good light color and strong carrier transport ability, and such high-performance undoped organic electroluminescent materials are very rare, so it is urgent to invent an organic solid non-doped A hybrid electroluminescent material and a corresponding organic electroluminescent device.
  • the technical problem to be solved by the present invention is to provide an organic electroluminescent material and a corresponding organic electroluminescent device, which are simple in preparation, high in yield, good in thermodynamic stability, capable of covering visible light regions, and having good electroluminescence.
  • a luminescent effect and an undoped organic electroluminescent device can be prepared.
  • one technical solution adopted by the present invention is to provide an organic electroluminescent material having a molecular formula of Da- ⁇ -Ac, wherein Da is an aggregation-inducing luminescent group, and ⁇ is a conjugated bond. And Ac is a strong electron withdrawing group;
  • the Da has the following structural formula:
  • R1 is a direct single bond or an aromatic ring
  • R2 is a hydrogen atom or a benzene ring
  • R3 and R4 are each selected from at least one of a hydrogen atom, a C1-8 alkyl group, a C1-4 alkyl group, an aryl group, and a carbazolyl group. ;
  • R5 is selected from C1 ⁇ 5 alkyl group or a nitro group (-NO 2).
  • the organic electroluminescent material is produced by reacting an aggregation-inducing luminescent group having an aromatic aldehyde with a strong electron-withdrawing group having a reactive methyl group in a weak alkali environment,
  • R1 is a direct single bond or an aromatic ring
  • R2 is a hydrogen atom or a benzene ring
  • R3 and R4 are each selected from the group consisting of a hydrogen atom, a C1-8 alkyl group, a C1-4 alkyl group, an aryl group, and a carbazolyl group. at least one.
  • the organic electroluminescent material is produced by reacting an aggregation-inducing luminescent group having an aromatic aldehyde with a strong electron-withdrawing group having an amino group in a weak acid environment.
  • R1 is a direct single bond or an aromatic ring
  • R2 is a hydrogen atom or a benzene ring
  • R3 and R4 are each selected from the group consisting of a hydrogen atom, a C1-8 alkyl group, a C1-4 alkyl group, an aryl group, and a carbazolyl group. at least one.
  • another technical solution adopted by the present invention is to provide an organic electroluminescent material having a molecular formula of Da- ⁇ -Ac, wherein Da is an aggregation-inducing luminescent group, and ⁇ is a conjugate. Key, while Ac is a strong electron withdrawing group.
  • R1 is a direct single bond or an aromatic ring
  • R2 is a hydrogen atom or a benzene ring
  • R3 and R4 are each selected from at least one of a hydrogen atom, a C1-8 alkyl group, a C1-4 alkyl group, an aryl group, and a carbazolyl group. .
  • R5 is selected from C1 ⁇ 5 alkyl group or a nitro group (-NO 2).
  • the organic electroluminescent material is produced by reacting an aggregation-inducing luminescent group having an aromatic aldehyde with a strong electron-withdrawing group having a reactive methyl group in a weak alkali environment,
  • the organic electroluminescent material is produced by reacting an aggregation-inducing luminescent group having an aromatic aldehyde with a strong electron-withdrawing group having an amino group in a weak acid environment.
  • an organic electroluminescent device comprising: a substrate; and an anode, a hole transport layer, a light emitting layer, and an electron sequentially disposed on the substrate a transport layer and a cathode; wherein the light-emitting layer has a molecular formula of Da- ⁇ -Ac, Da is an aggregation-inducing luminescent group, ⁇ is a conjugated bond, and Ac is a strong electron-withdrawing group.
  • the beneficial effects of the present invention are that the preparation method of the organic electroluminescent material of the present invention is simple, and all the raw materials can be obtained in high yield, unlike the case of the prior art. Further, since the electroluminescent material of the present invention contains a plurality of benzene rings in its skeleton, it can exhibit relatively high thermodynamic stability.
  • the molecular structure of Da- ⁇ -Ac can effectively produce a fluorescent material covering the visible light region. Such a molecular structure can generate strong fluorescence in a solid state and has a good electroluminescence effect.
  • the non-doped organic electroluminescent device is prepared to avoid the influence of doping concentration, enhance the stability and repeatability of the device, effectively extend the life of the device, and reduce the difficulty of the processing process, and is suitable for large-scale Commercial production.
  • Figure 1 is a schematic view of an organic electroluminescent device according to an embodiment of the present invention.
  • the present invention provides an organic solid non-doped electroluminescent material having a molecular formula of Da- ⁇ -Ac, wherein Da is an aggregation-inducing luminescent group, ⁇ is a conjugated bond, and Ac is a strong electron-withdrawing electron. Group.
  • Da can adopt the following structural formula:
  • R1 is a direct single bond or an aromatic ring
  • R2 is a hydrogen atom or a benzene ring
  • R3 and R4 are each selected from at least one of a hydrogen atom, a C1-8 alkyl group, a C1-4 alkyl group, an aryl group, and a carbazolyl group. .
  • Da may be selected from any one of the following structures:
  • R5 is selected from C1 ⁇ 5 alkyl group or a nitro group (-NO 2).
  • the molecular formula of the organic electroluminescent material may be selected from any of the following structures. One of the meanings:
  • R1 is a direct single bond or an aromatic ring
  • R2 is a hydrogen atom or a benzene ring
  • R3 and R4 are each selected from a hydrogen atom, a C1-8 alkyl group, a C1-4 alkyloxy group, an aryl group and a carbazolyl group. At least one
  • R5 is selected from a C 1-5 alkyl group or a nitro group (-NO 2 ).
  • the organic electroluminescent material of the present invention can be produced by reacting an aggregation-inducing luminescent group having an aromatic aldehyde with a strong electron-withdrawing group having a reactive methyl group in a weak alkali environment, and the reaction formula is as follows:
  • the organic electroluminescent material of the present invention can also be produced by reacting an aggregation-inducing retroreflective group having an aromatic aldehyde with a strong electron-withdrawing group having an amino group in a weak acid environment, and the reaction formula is as follows:
  • Da may be a tetrastyrene or tristyrene derivative containing an aromatic aldehyde, thereby allowing the aromatic aldehyde to react with the active methyl group or react with the amino group to prepare a good thermal stability and solid state.
  • a quantum yield of a compound of the ALE- ⁇ -strong electron withdrawing group structure may be a tetrastyrene or tristyrene derivative containing an aromatic aldehyde, thereby allowing the aromatic aldehyde to react with the active methyl group or react with the amino group to prepare a good thermal stability and solid state.
  • the compound of this structure is introduced by the conjugate of a strong electron-withdrawing group, its electron affinity is significantly increased, the intramolecular charge transfer is enhanced, the band gap of the molecule is adjusted, and the light absorption and emission range of the molecule are broadened. It is an electroluminescent material that can efficiently inject and transport both holes and electrons with excellent performance.
  • the present invention further provides an organic electroluminescent device prepared using the organic electroluminescent material as described above.
  • Figure 1 is a schematic illustration of an organic electroluminescent device of the present invention.
  • the organic electroluminescent device 100 of the present invention includes a substrate 110, an anode 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and a cathode 160.
  • the anode 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the cathode 160 are sequentially disposed on the substrate 110.
  • the anode 120 may be made of ITO (indium tin oxide); the hole transport layer 130 may be NPB (N,N'-bis(1-naphthyl)-N,N'-diphenyl-1, 1'-biphenyl-4-4'-diamine); the light-emitting layer 140 can be made of the above-mentioned organic electroluminescent material having a Da- ⁇ -Ac structure; the electron transport layer 150 can be made of Alq3 It is made of (tris(8-hydroxyquinoline)aluminum) material; the cathode 160 can be made of LiF (lithium fluoride) or Al (aluminum).
  • the preparation method of the organic electroluminescent material of the present invention is simple, and all raw materials can be obtained in high yield. Further, since the electroluminescent material of the present invention contains a plurality of benzene rings in its skeleton, it can exhibit relatively high thermodynamic stability.
  • the molecular structure of Da- ⁇ -Ac can effectively produce a fluorescent material covering the visible light region. Such a molecular structure can generate strong fluorescence in a solid state and has a good electroluminescence effect. Therefore, the use of such a material can
  • the non-doped organic electroluminescent device is prepared to avoid the influence of doping concentration, enhance the stability and repeatability of the device, effectively extend the life of the device, and reduce the difficulty of the processing process, and is suitable for large-scale Commercial production.

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Abstract

本发明公开了提供一种有机电致发光材料，其分子通式为Da-π-Ac，其中，Da为聚集诱导发光基团，π为共轭键，而Ac为强吸电子基团。本发明的有机电致发光材料制备方法简单，产率较高，热力学稳定性好，能够覆盖可见光区域，具有良好的电致发光效果，且能制备出非掺杂型的有机电致发光器件。

Description

有机电致发光材料及有机电致发光器件 【技术领域】
本发明涉及显示技术领域，特别是涉及一种有机电致发光材料及相关的有机电致发光器件。
【背景技术】
随着科技的发展，人们对于显示装置的对比度、色彩变化、分辨率、成本、能耗和质量等，都提出了越来越高的要求。液晶显示装置由于能耗高、成本高等各种缺点，已经越来越难以满足人们的要求了，而有机电致发光(Organic Light-Emitting Diode，OLED)技术获得了极大地发展，其具有主动发光、低压直流驱动、全视角、响应速度快、工作温度范围宽和可柔性显示等优点，因此，有机电致发光显示器替代液晶显示器，已经成为科技发展的大趋势。
在有机电致发光技术中，有机电致发光材料的选择至关重要，其性质是决定器件性能的关键因素之一。目前，有机电致发光材料大致主要采用有机小分子化合物或聚合物，其具有化学修饰性强、选择范围广、易于提纯、荧光量子效率高和可以产生红、绿、蓝等各种颜色广的特定。
大多数的有机染料在固态时存在浓度淬灭的问题，其将导致器件的发射峰变宽、光谱红移、荧光量子效率下降等缺陷，因此，一般将它们以最低浓度的方式掺杂在具有某种载流子性质的主体中，用能量传递的原理将微量的有机荧光染料分散在主发光体的矩阵中，从而使客体分子可通过激发光能的传递而发光。因此，目前报道的高性能的有机电致发光器件大多采用了发光层掺杂的制备方法。
但是，这种掺杂的制备方法需要精密地调控以确保掺杂浓度的准确，这将提高制作成本，不利于有机电致发光技术的产业化。同时，掺杂器件中主客体的相分离和能量转移也会影响器件的性能和稳定性。
因此，相比于有机电致发光掺杂型器件，有机电致发光非掺杂型器件可以避免掺杂浓度的影响，其增强了器件的稳定性和可重复性，有效地延长了器件的寿命，降低了加工工艺的难度，适合大规模地商业化生产。但是，在有机电致发光非掺杂型器件中，高性能的非掺杂的发光材料需要同时具备高效率固态 发光、良好的光色以及较强的载流子传输能力等这些苛刻的特性，而这种高性能的非掺杂的有机电致发光材料十分稀少，因此，急需发明一种有机固态的非掺杂的电致发光材料及相应的有机电致发光器件。
【发明内容】
本发明主要解决的技术问题是提供一种有机电致发光材料及相应的有机电致发光器件，其制备方法简单，产率较高，热力学稳定性好，能够覆盖可见光区域，具有良好的电致发光效果，且能制备出非掺杂型的有机电致发光器件。
为解决上述技术问题，本发明采用的一个技术方案是：提供一种有机电致发光材料，其分子通式为Da-π-Ac，其中，Da为聚集诱导发光基团，π为共轭键，而Ac为强吸电子基团；
所述Da具有如下结构通式：
Figure PCTCN2016088498-appb-000001
R1为直接单键或芳香环；R2为氢原子或苯环；而R3和R4分别选自氢原子、C1～8烷基、C1～4烷氧基、芳香基和咔唑基中的至少一个；
而所述Ac选自以下结构中的一种：
Figure PCTCN2016088498-appb-000002
其中，R5选自C1～5烷基或者硝基(-NO2)。
其中，所述Da选自以下结构中的一种：
Figure PCTCN2016088498-appb-000003
Figure PCTCN2016088498-appb-000004
其中，所述有机电致发光材料通过具有芳香醛的聚集诱导发光基团与具有活性甲基的强吸电子基团在弱碱环境下反应而制成，
Figure PCTCN2016088498-appb-000005
其中，R1为直接单键或芳香环；R2为氢原子或苯环；而R3和R4分别选自氢原子、C1～8烷基、C1～4烷氧基、芳香基和咔唑基中的至少一个。
其中，所述有机电致发光材料通过具有芳香醛的聚集诱导发光基团与具有氨基的强吸电子基团在弱酸环境下反应而制成，
Figure PCTCN2016088498-appb-000006
其中，R1为直接单键或芳香环；R2为氢原子或苯环；而R3和R4分别选自氢原子、C1～8烷基、C1～4烷氧基、芳香基和咔唑基中的至少一个。
为解决上述技术问题，本发明采用的另一个技术方案是：提供一种有机电致发光材料，其分子通式为Da-π-Ac，其中，Da为聚集诱导发光基团，π为共轭键，而Ac为强吸电子基团。
其中，所述Da具有如下结构通式：
Figure PCTCN2016088498-appb-000007
R1为直接单键或芳香环；R2为氢原子或苯环；而R3和R4分别选自氢原子、C1～8烷基、C1～4烷氧基、芳香基和咔唑基中的至少一个。
其中，所述Da选自以下结构中的一种：
Figure PCTCN2016088498-appb-000008
其中，所述Ac选自以下结构中的一种：
Figure PCTCN2016088498-appb-000009
其中，R5选自C1～5烷基或者硝基(-NO2)。
其中，所述有机电致发光材料通过具有芳香醛的聚集诱导发光基团与具有活性甲基的强吸电子基团在弱碱环境下反应而制成，
Figure PCTCN2016088498-appb-000010
其中，所述有机电致发光材料通过具有芳香醛的聚集诱导发光基团与具有氨基的强吸电子基团在弱酸环境下反应而制成，
Figure PCTCN2016088498-appb-000011
其中，所述有机电致发光材料的分子式选自以下结构中的一种：
Figure PCTCN2016088498-appb-000012
为解决上述技术问题，本发明采用的又一个技术方案是：提供一种有机电致发光器件，其包括：基板；以及依次设置在所述基板上的阳极、空穴传输层、发光层、电子传输层和阴极；其中，所述发光层的分子通式为Da-π-Ac，Da为聚集诱导发光基团，π为共轭键，而Ac为强吸电子基团。
本发明的有益效果是：区别于现有技术的情况，本发明的有机电致发光材料的制备方法简单，且所有的原材料都能以高产率而获得。此外，由于本发明的电致发光材料的骨架中含有多个苯环，因此其能够呈现出比较高的热力学稳定性。而Da-π-Ac的分子结构可以有效地制造出覆盖可见光区域的荧光材料，这类分子结构在固态下能够产生很强的荧光，具有良好的电致发光效果，因此，采用此种材料能够制备出非掺杂型的有机电致发光器件，从而避免掺杂浓度的影响，增强器件的稳定性和可重复性，有效地延长了器件的寿命，降低了加工工艺的难度，适合大规模的商业化生产。
【附图说明】
图1是本发明一实施例所示的有机电致发光器件的示意图。
【具体实施方式】
下面结合附图和实施方式对本发明进行详细说明。
本发明提供一种有机固态的非掺杂的电致发光材料，其分子通式为Da-π-Ac，其中，Da为聚集诱导发光基团，π为共轭键，而Ac为强吸电子基团。
其中，Da可以采用如下的结构通式：
Figure PCTCN2016088498-appb-000013
R1为直接单键或芳香环；R2为氢原子或苯环；而R3和R4分别选自氢原子、C1～8烷基、C1～4烷氧基、芳香基和咔唑基中的至少一个。
在本发明的实施例中，Da可以选自以下结构中任意之一：
Figure PCTCN2016088498-appb-000014
而Ac可以选自以下结构中任意之一：
Figure PCTCN2016088498-appb-000015
其中，R5选自C1～5烷基或者硝基(-NO2)。
在本发明实施例中，有机电致发光材料的分子式可以选自以下结构中的任 意之一：
Figure PCTCN2016088498-appb-000016
其中，，R1为直接单键或芳香环；R2为氢原子或苯环；R3和R4分别选自氢原子、C1～8烷基、C1～4烷氧基、芳香基和咔唑基中的至少一个；而R5选自C1～5烷基或者硝基(-NO2)。
本发明的有机电致发光材料可以通过具有芳香醛的聚集诱导发光基团与具有活性甲基的强吸电子基团在弱碱环境下进行反应而制成，其反应式如下：
Figure PCTCN2016088498-appb-000017
或者，本发明的有机电致发光材料也可以通过具有芳香醛的聚集诱导反光基团与具有氨基的强吸电子基团在弱酸环境下进行反应而制成，其反应式如下：
Figure PCTCN2016088498-appb-000018
在本发明实施例中，Da可以选用含有芳香醛的四笨乙烯或者三苯乙烯衍生物，从而让芳香醛与活性甲基进行反应或者与氨基进行反应，从而制备出具有良好热稳定性和固态量子产率的ALE-π-强吸电子基团结构的化合物。
这种结构的化合物由于强吸电子基团的共轭引入，其电子亲和势显著增加，分子内电荷转移增强，对分子的带隙进行了调节，扩宽了分子的光吸收和发射范围等，成为空穴和电子都能够高效注入和传输、性能优良的电致发光材料。
本发明进一步提供一种采用如上所述的有机电致发光材料制备的有机电致发光器件。图1是本发明的有机电致发光器件的示意图。如图1所示，本发明的有机电致发光器件100包括基板110、阳极120、空穴传输层130、发光层140、电子传输层150和阴极160。其中，阳极120、空穴传输层130、发光层140、电子传输层150和阴极160依次地设置在基板110上。
其中，阳极120可以采用ITO(氧化铟锡)材质而制成；空穴传输层130可以采用NPB(N，N′-二(1-萘基)-N，N′-二苯基-1，1′-联苯-4-4′-二胺)材质而制成；发光层140可以采用上述的具有Da-π-Ac结构的有机电致发光材料而制成；电子传输层150可以采用Alq3(三(8-羟基喹啉)铝)材质而制成；阴极160可以采用LiF(氟化锂)或者Al(铝)材质而制成。
本发明的有机电致发光材料的制备方法简单，且所有的原材料都能以高产率而获得。此外，由于本发明的电致发光材料的骨架中含有多个苯环，因此其能够呈现出比较高的热力学稳定性。而Da-π-Ac的分子结构可以有效地制造出覆盖可见光区域的荧光材料，这类分子结构在固态下能够产生很强的荧光，具有良好的电致发光效果，因此，采用此种材料能够制备出非掺杂型的有机电致发光器件，从而避免掺杂浓度的影响，增强器件的稳定性和可重复性，有效地延长了器件的寿命，降低了加工工艺的难度，适合大规模的商业化生产。
以上所述仅为本发明的实施方式，并非因此限制本发明的专利范围，凡是利用本发明说明书及附图内容所作的等效结构或等效流程变换，或直接或间接运用在其他相关的技术领域，均同理包括在本发明的专利保护范围内。

Claims (7)

  1. 一种有机电致发光材料，其中，所述有机电致发光材料的分子通式为Da-π-Ac，其中，Da为聚集诱导发光基团，π为共轭键，而Ac为强吸电子基团；
    所述Da具有如下结构通式：
    Figure PCTCN2016088498-appb-100001
    其中，R1为直接单键或芳香环；R2为氢原子或苯环；而R3和R4分别选自氢原子、C1～8烷基、C1～4烷氧基、芳香基和咔唑基中的至少一个；
    而所述Ac选自以下结构中的一种：
    Figure PCTCN2016088498-appb-100002
    其中，R5选自C1～5烷基或者硝基(-NO2)。
  2. 根据权利要求1所述的有机电致发光材料，其中，所述Da选自以下结构中的一种：
    Figure PCTCN2016088498-appb-100003
  3. 根据权利要求1所述的有机电致发光材料，其中，所述有机电致发光材料通过具有芳香醛的聚集诱导发光基团与具有活性甲基的强吸电子基团在弱碱 环境下反应而制成，
    Figure PCTCN2016088498-appb-100004
    其中，R1为直接单键或芳香环；R2为氢原子或苯环；而R3和R4分别选自氢原子、C1～8烷基、C1～4烷氧基、芳香基和咔唑基中的至少一个。
  4. 根据权利要求1所述的有机电致发光材料，其中，所述有机电致发光材料通过具有芳香醛的聚集诱导发光基团与具有氨基的强吸电子基团在弱酸环境下反应而制成，
    Figure PCTCN2016088498-appb-100005
    其中，R1为直接单键或芳香环；R2为氢原子或苯环；而R3和R4分别选自氢原子、C1～8烷基、C1～4烷氧基、芳香基和咔唑基中的至少一个。
  5. 一种有机电致发光材料，其中，所述有机电致发光材料的分子通式为Da-π-Ac，其中，Da为聚集诱导发光基团，π为共轭键，而Ac为强吸电子基团。
  6. 根据权利要求5所述的有机电致发光材料，其中，所述Da具有如下结构通式：
    Figure PCTCN2016088498-appb-100006
    其中，R1为直接单键或芳香环；R2为氢原子或苯环；而R3和R4分别选自氢原子、C1～8烷基、C1～4烷氧基、芳香基和咔唑基中的至少一个。
  7. 根据权利要求6所述的有机电致发光材料，其中，所述Da选自以下结构中的一种：
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